N-bromobutanimide → 1-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1741045Notes

Reaction equation

HRID 1741045 reaction equation
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>CC(O)=O.C(OCC)(=O)C>[C:1]([N:4]1[C:10]2[CH:11]=[C:12]([Br:16])[C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 218338251-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 218338021-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepineYield 31%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine (D24, 2.81 g, 14 mmol) was stirred in glacial AcOH (50 ml) as N-bromosuccinimide (2.69 g, 15 mmol) was added portionwise over 20 min. The mixture was stirred for 30 min, diluted with ethyl acetate (500 ml), washed with water, K2CO3 solution and brine, dried (Na2SO4) and evaporated to give a tan solid, shown by NMR and TLC to be a mixture of dibromo and mono-bromo isomers. Chromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane, yielded pure title compound (1.22 g, 31%) as a cream solid.

Workup

  1. additionwas added portionwise over 20 min
  2. washwashed with water, K2CO3 solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a tan solid
  6. additiona mixture of dibromo and mono-bromo isomers
  7. washChromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-7346bbfc15064b649313c71b761e3bb1
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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